You’re sure to have a blast at any one of the Annual Events happening in the Florida Keys

I think several of the annual events will convince you that it helps to be a little crazy to live in the Florida Keys. We’ll use any excuse to throw a party and invite the whole country.

I want to give you a sampling of the annual Florida Keys style events. I’ll start with January in the Upper Keys and work my way down with each month. Keep in mind that some dates and locations change from year to year.


In the Upper Keys the Holiday Isle has a party going on every day and night. They also have The Holiday Isle Sailfish Tournament, Sailboat Competition and the Grid Iron Fishing Tournament. All in January.

back yard in Key West

The Cheeca Lodge Presidential Sailfish Tournament is a catch and release tournament. It’s held in January. It’s named for George W. Bush who fishes the waters of Islamorada in this annual event.

The Key West Craft Show is a week long event held the last week in January. Exhibitors come from all over the country with their hand made crafts. ( Any excuse to get away from the cold.) It’s held on Whitehead Street between Eaton and Greene Street. It’s free.

Old Island Days House and Garden Tours in Key West. This annual event is a self-guided tour. It’s actually held January, February, and March. Usually their will be 5 or 6 private properties in the tour. The idea is to encourage preservation of Key West’s historical homes.

Key West Literary Seminar is held at the San Carlos Institute on Duval Street. You’ll need to plan this one way in advance, this annual event usually sold out the year before it’s held. It’s in the second week of January and is a four day event. There are writing workshops, tours of local authors homes and parties.

Sailboat off Key West

Key West Race Week brings in a lively bunch of racers. Anyone who’s into sailing is at this regatta. It’s the largest annual regatta in the Country. There will be more than 300 sailboats in the regatta. This one’s for fame and glory, not for money. America’s Cup Teams use this one for practice. Seems we always have strong cold north winds for this annual event.


Holiday Isle hosts an Antique Car Show, the Sweethearts Arts ‘n Crafts Festival as well as the Poor Girls Sailfish Tournament.

In Marathon the Pigeon Key Art Festival is held on Pigeon Key. That’s the little island at the end of the functioning span of the Old Seven Mile Bridge. 70 Artists are chosen from hundreds who compete to display their art in the show. There’s live entertainment with all different types of music. The local restaurants are there in case for work up an appetite. You can come by boat to this annual event.

The Florida Keys Outdoor Art Show is at Key Colony Beach Park. This is usually held in February but sometimes is moved to March.

Old Island Days Art Festival is on Whitehead Street in Key West. It stretches from Greene to Caroline Street and spills over into Truman Annex. The artists are local Key’s Artists. You’ll know this is true as soon as you see the explosive colors they choose.

Commercial Fishermen MARCH

In March Holiday Isle revs up the spring breakers by holding a Bikini Contests and Body Building Competition.

Marathon invites you to taste great fresh local seafood at The Original Marathon Seafood Festival. The local commercial fisherman are part of this annual event. There’s a flea market with marine items, live entertainment and a raffle. This is one the whole family will enjoy.

Heritage Days are held at Fort Zachary Taylor State Historical Site. It’s at Truman Annex at Southard Street in Key West. It’s a re-creation of what it was like to live in the Civil War Days in a fort. They’re all dressed up in costume. The fort was union occupied throughout the war even though Key West had seceded from the Union. That was the first time Key West seceded, but not the last.

My Pitcher plant Key West Garden Club Flower Show is held at West Martello Tower. This is held every other year. The show has been established for 58 years. This is a big show with 700 to 800 entries. The Orchid Society holds a show at the West Martello Tower on the other year. Once again sometimes they do this in April.

It's time again for the St. Patty’s Day Bar Stroll. I’ve enjoyed this one many years. Six to seven hundred people flow thru the streets of Key West forced to drink a beer at several planned stops. This annual event is great fun.

Key West holds a Conch Shell Blowing Contest. Its at the Sunset Pier at Ocean Key House at the end of Duval Street. You get prizes for being crazy here. They judge the loudest, funniest and the most entertaining conch shell blower. Sometimes this is moved to April. It’s really funny to watch.

Seven Mile Bridge sign


For Easter the Holiday Isle hosts a Kids Day Easter Egg Hunt. The Cheeca Lodge welcomes everyone to Earth Day at Cheece Lodge. It’s a grand event. There’s a fishing tournament, live entertainment and lots of barbecues. The proceeds go towards Mother Earths needs.

A Taste of Islamorada is where the restaurants of the Upper Keys get to show of their creative tasty dishes. There’s at least 20 restaurants represented here. Live music entertains you as you munch down of the great food that’s here for the sampling.

The Seven Mile Bridge run is held each year in April. It’s the only run held completely over water. What a view the runners enjoy. There are only 1500 runners allowed, and it fills up fast. As of 2012 the runners get their entry forms via the internet. A huge party follows along with the awards presentation. This annual event is the favorite for many runners. The run was canceled in 2012 due to thunder and lightning moving through the Keys.

The Conch Republic Independence is celebrated for a the entire week with April 23 being the actual day Key West seceded from the rest of the country. Activities range from a bed race down Duval Street to a battle on the water with food as the ammo. It’s easy to get caught up in this crazy annual event.

A Taste of Key West is at Higgs Beach where White Street and Atlantic Boulevard meet. This is a fantastic opportunity to get a sample of the very best Key West Restaurants have to offer. There are over 100 restaurants represented here. And there all right there in one place. I highly recommend this annual event.

The Shell Key West Classic. This is when the serious fishermen with serious money join in and have a great time for a great cause. Prizes are big bucks.

Holiday Isle in Islamorada


The Upper Keys at Holiday Isle host a Hospitality Expo. It's the Memorial Day Celebration at the end of the month. Thousands descend upon the Upper Keys at the Sandbar just off Holiday Isle. Boats of all kinds can be seen. The Monroe County Sheriff keeps a close eye on the boaters. Some imbibe in too much alcohol and tend to get a bit rowdy. Rumors were circulating this year suggesting it was the last year for this big happening. The Holiday Isle has new owners that were going to demolish the place and put up condo's. Well I was just up there and spoke with my friend Trapper John, he told me this plan has been put on hold. The slowing real estate market has caused them to change their plan for now. They're going to spruce the place up a bit and carry on with business as usual.

The Key West Songwriters Fest is a four day event. It’s at the Hog’s Breath Saloon. It brings some of the best performing songwriters to the stage. The place is always packed. You’ll need to get there early for a seat to this annual event.

The Marathon Offshore Grand Prix Powerboat Race takes place in the waters around the Seven Mile Bridge. These boats are world class high speed racers.

Key West Old Island Day go all month long from May 1 thru May 31.

Tarpon swimming JUNE

Hurricane season begins. This annual event we would love to cancel. It's not celebrated with a party or a parade.

Islamorada hosts the Don Hawley Invitational Tarpon Tournament. They fly fishing for Tarpon. It’s the original all release tournament.

In Marathon the Nature Conservancy’s annual Native Plant Fair. There are presentations on Keys-friendly landscaping, butterfly gardens and lots more.

The Cuban American Heritage Festival is in Key West. This lasts for four days. A street fair, fishing tournament, salsa bands, cigar dinners, and a domino tournament are but part of the fun. At the same time you can attend a three day symposium at San Carlos Institute on Duval.

Mermaid at Underwater Music Festival


Fourth of July fireworks and celebration are at Bayside in Key Largo, Sombrero Beach in Marathon, Sugarloaf Airstrip in Sugarloaf, Casa Marina and the White Street Pier in Key West. Food, fun and live music are all a part of the celebrations.

The Reporter’s Fourth of July Parade closes US Highway 1 down for an hour from mile marker 98 to mile marker 101. It usually begins around ten in the morning.

The Underwater Music Festival Annual Event happens at Looe Key Reef . You’ll need a boat for this one. Music is played underwater and is broadcast on US 1 Radio, 104.1 FM from ten until four. Dive swim or snorkel while listening to the music. Elvis plays unplugged while mermaids swim to the music. Lubell lab made the special speakers for the festival. We’re minus one speaker this year, Hurricane Wilma destroyed it.

Hemingway Days are always in July. Hemingway Days Festival begins at the Hemingway Home and Museum. Next is the Drambuie Key West Marlin Tournament. The Captains meeting is at the Conch Republic Seafood Restaurant. Last is the Papa Hemingway look-alike contest at Sloppy Joe’s Bar. You can also enjoy readings and presentations, Caribbean Street Fair, dockside cocktail party, 100+ birthday party for Papa, Running of the Bulls and a whole lot more. So rest up, this annual event goes for ten days.

Lobster Becky and me Lobster Sport Mini-Season is the last Wednesday and Thursday in July. This is another annual event that we would love to see canceled. People come from all over to chase these spiny creatures into their nets. Special regulations apply for this two day season.

Reef Awareness Week ends the month with a week long awareness drive. The theme this year is Protect Endangered Coral Reefs. This is a great cause and close to most of us living in the Florida Keys where we are very aware of our reef’s health. You’re invited to join in this most worthy event.


Regular Lobster season begins on August 6 of each year. The season ends on March 31. Lets do the math, this means you have right at 8 months to dive for lobster. You can grab a lots of them in that much time.

Islamorada Swordfish Tournament is a challenging tournament. The fish have to be at least 60 inches long to qualify. It’s a modified release tournament.

The Mercury Redbone is fished in the waters of the Lower Keys.


The Florida Keys Poker Run begins in Miami and ends in Key West. More than 10,000 motorcycles run up and down the Overseas Highway stopping at various locations to pick up playing cards. The player with the highest poker hand wins. This annual event makes for a loud time in the Keys. There are noise ordinances on the books concerning the excessive noise level in Key West. I don’t think anyone bothered to read that one.

WomanFest is a Key West only event. Dinners, cocktail parties, watersports, wine-tasting and sunset sails are just a few of the activities. Key West has always been a popular place for Gays and Lesbians to gather.

The Redbone Mercury Celebrity SLAM in Key West is first in series. Anglers try to catch bonefish , permit and tarpon in one day for a Grand Slam. This annual event is scheduled each September.

The first ever Lionfish Derby for Divers will be held on September 11, 2010 at Coconuts in Key Largo. No limits, just kill all you can for cash. Three of these tournaments are held each year throughout the Keys.


Key Largo hosts the Baybone Mercury Celebrity Tournament at the Westin Beach Resort. This is the second in the Celebrity Tournament Series. The targeted fish are the permit and the bonefish. It’s a catch-and-release tournament.

The second Lionfish Derby in the Florida Keys is going to be in Marathon at Keys Fisheries. No size limit and no limit to how many you can shoot. There's $3000 in prizes and a chance to win $10,000.

Me and Vera at Fantasy Fest

The Annual Key West Fantasy Fest is always the last full week in October. This year's theme is “A-Conch-Alypse.” This is our version of Mardi Gras. Over 80,000 people attend from all over the globe. Some of the costumes can be a little tough on your eyes. It’s more lots more fun if you’re in costume. Here's a great place to find your Adult Halloween Costumes. at

Goombay Festival is a street party in Bahama Village in Key West. This is a two day event. The focus is on the Bahamian culture which is so much a part of Key West it’s foods and colors. Calypso Bands and Steel Drums play Caribbean music to get you dancing in the streets.


George Bush Cheeca Lodge Bonefish Tournament is held at Cheeca Lodge. George H. Bush comes to enjoy fishing the waters of the back country of the Upper Keys.

Costumes under $30

Sky Dive Marathon is held at the Marathon Airport with more than 160 skydivers from all over the country. There’s also an air show and it’s free.

The Meeting of the Minds is when Jimmy Buffets most loyal fans gather in Key West to celebrate being a Parrothead. These guys definitely know how to party. I love their head gear.

Offshore Powerboats The Key West Offshore World Championships power boat racing are coming this month. These are the big boats that reach speeds on the water of 125 to 150 mph. The helicopters that accompany these boats make the race that much more exciting. It’s a thrill to watch the boats blasting thru the harbor.

The third Lionfish Derby for Divers will be held in November at Hurricane Hole Marina on Stock Island. Please join us in trying to eliminate this invasive species from the waters of the Florida Keys.

Cayo Carnival is held at East Martello Museum. It benefits Reef Relief. Lots of great food from some of Key West’s finest restaurants. There’s also lots of local bands for those who love to dance.

Helicoptors over race boats


Christmas Boat Parades can be seen up and down the Keys. Bayside, Key Largos boats travel thru Blackwater Sound with over 30 boats decorated with lights. Key Colony Beach has it’s boat parade thru the canals of Key Colony Beach. It’s just as spectacular at the one in Key Largo. Boot Key Harbor in Marathon holds a boat parade each year and can be viewed best from the Boot Key Harbor Bridge, Faro Blanco or The Dockside Lounge on Sombrero Road. Key West has a boat parade. It begins as the Schooner Wharf Bar and travels around thru the harbor then back. Folks on land, and anchored boats get to enjoy the beautifully lighted boats participating in this annual event.

The Redbone Mercury Cheeca Celebrity Tournament is the third in the Celebrity Series. This annual event is held at the Cheeca Lodge. The targeted fish are the redfish and the bonefish.

Christmas Around the World at Marathon Garden Club shows off their skills in decorating more that a dozen trees. They’re decorated in traditional styles from many countries. The trees are beautiful.

Key West New Year’s Eve Celebration is on Duval Street. It’s a huge party and its shown live on CNN. You have your choices of things being lowered to mark the New Year’s arrival. A big Conch Shell lowered from the top of Sloppy Joe’s Bar. A Pirate Wench lowered from the mast of a Schooner in the Historic Seaport or lastly Sushi, a local drag queen lowered from balcony riding a gigantic Red high heel slipper.

Other events do happen throughout the Florida Keys. I’ll keep you up to date on those and any changes in the annual events in The Keys Blog.

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